You can find tons of great deals and styles by tirelessly rummaging through vintage/Goodwill stores, but unearthing them means you'd have to become the kind of person that tirelessly rummages through vintage/Goodwill stores. Let a couple girls do the digging for you, with ShopBar
ShopBar's run by two easy-on-the-eyes ladies majoring in fashion merchandising at the Art Institute, who every week scour the hinterlands of Dade and Broward for vintage stuff they think "would look hot on some dude", then curate it all in a weekly popup store inside Black Sheep bar, where you can shop, play pool, and snag well drinks at 3/$10, which basically makes it Goodwill booze. While the one-off stock's obviously in constant flux, finds so far include tees like one in bright blue with a manatee, dolphins, and a sea turtle all happily swimming together in shafts of sunlight, a way-old, contrast-stitched number with a pic of Rocky in lumpy sweats atop the stairs in Philly, and one with a pretty rainbow and the phrase "Open Books, Open Minds" -- which is exactly what the lefty communist LeVar Burton would want you to believe. So far, they've also dug up vintage cowboy shirts, grungy flannels, fancier stuff like Christian Dior & Calvin Klein dress shirts, a bevy of Members Only jackets, and a shiny aqua/black Dior track jacket that'd look at home in a breakdancing vid, on grandpa with his metal detector in Boca, or on you, burying cans on the beach just to keep grandpa out of your hair
There's not a lot of pants, "'cause guys are too lazy to try them on", but Shop's got ties of the skinny and bow varieties, as well as shorts, like some circa-1987 Izod tennis jobs ideal for your John McEnroe look, which'll have people saying, "That came from Goodwill?!? You cannot be serious!!!".